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Chemistry 3719 - Organic Chemistry I

• Professor Dr. Peter Norris• Office 6014 Ward Beecher• Telephone (330) 941-1553• Email pnorris@cc.ysu.edu • Website http://www.as.ysu.edu/~pnorris/

public_html• Lab Coord. Dr. John Jackson• Office 5009 Ward Beecher• Telephone (330) 941-1551

Chemistry Computer LabNorth end of Ward Beecher on the 5th floor

24 600 MHz Pentium machines (Gateway)

2 Hewlett Packard network laserjet printers

1 Student assistant

All PC’s have MS Office, ChemDraw, ChemSketch, ACD NMR prediction software, Spartan molecular modeling package, Netscape Navigator and MS Internet Explorer

Open 9-5 Mon through Fri (see lab door for schedule)

www.adobe.com

Free Adobe Acrobat Reader

What is Organic Chemistry?

The study of the compounds that contain carbon and the reactions of those materials (millions known)

Why a whole year of Organic?

Carbon can bond in multiple ways to form a huge number of different molecules, and these compounds form the basis of many different disciplines, e.g.:

Biology (DNA, proteins, carbohydrates)

Medicine and Pharmaceuticals (Aspirin, Taxol, AZT)

Chemical Engineering (oil, plastics, fine chemicals)

Timeline1807 Berzelius introduces the term “Organic Chemistry” to describe the

study of compounds isolated from nature.

1828 Wohler makes urea, the first natural organic compound to be

synthesized in the laboratory.

1890 Fischer studies the chemistry of proteins, carbohydrates and the

nucleic acids.

1950 Woodward and Eschenmoser complete the first total synthesis of

Vitamin B12.

1990 Kishi, Nicolau, Smith, Schreiber, etc. complete total syntheses of

compounds such as Brevetoxin B, Taxol, etc.

2001 Schreiber, Dervan, etc. developing “Chemical Biology,” “Chemical

Genetics,” and “Chemical Proteomics” to study life processes.

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Organic Synthesis

Taxol Synthesis - 1996 Nicolau and Holton total syntheses ~60 synthetic steps in each

Starting material (cheap) Products (expensive)H2N

O

NH2

UREA - 1828

Palytoxin

Brevetoxin B

Chemistry 3719 and 3720 (and labs)

Lectures

• Structure and nomenclature of compounds and groups

• Physical properties and analysis of materials

• Reactivity and transformations with reagents

• Importance of organic compounds in society

Labs

• Glassware and equipment used to prepare organics

• Instrumentation used to analyze compounds

• Writing detailed reports of lab preparations

Organic Chemistry at YSU

• B.S. and M.S. degrees in Chemistry

• State of the art instrumentation (>$1,000,000 worth)

• Active research programs (Norris and Jackson)

• Student involvement in 3719/20, 4850, 6990

• Students present at regional and national meetings

• Undergrad and graduate students publish in journals

• Companies come to recruit our students

• Students move on to top graduate programs (Penn,

Wisconsin, Ohio State, Purdue, Penn State, UNC, UC-

Irvine, Pitt.)

YSU Students in Organic Chemistry

• Scott Freeze – Penn, 4th year Ph.D. Organic Chemistry

• Rob Cicchillo – Penn State, 3rd year Ph.D. Biochemistry

• Jason McCartney – UC Irvine, 2nd year Ph.D. Organic

• Dan Berndt – UNC Chapel Hill, 2nd year Ph.D. Biochemistry

• Chris Ciolli – Wisconsin Madison, 4th year Ph.D. Organic

• Chris Gabriel – Ohio State, 3rd year Ph.D. Organic

• Andy Fluxe – Medicinal Chemist, Procter and Gamble

• Hud Risley – Medicinal Chemist, Pfizer Pharmaceuticals

• Chris Meta – Pitt, 1st year Ph.D. Organic

Carey Chapter 1

Structure Determines Properties

• Atomic and electronic structure of atoms

• Ionic and covalent bonding

• Electronegativity and polar covalent bonds

• Structures of organic compounds - representations

• Resonance within molecules

• Shapes of molecules

• Molecular orbitals and orbital hybridization

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Periodic Table of the ElementsProbabil i ty distribution for an electron

Figure 1.1

Boundary surfaces of a 1s and 2s orbitalFigure 1.2 Boundary surfaces of the 2p orbitals

Figure 1.3

Electronic Structure of Atoms – Table 1.1

Atom Atomic No. Electronic Structure

H 1 1s1

He 2 1s2

Li 3 1s2 2s1

Be 4 1s2 2s2

B 5 1s2 2s2 2px1

C 6 1s2 2s2 2px1 2py1

N 7 1s2 2s2 2px1 2py1 2pz1

O 8 1s2 2s2 2px2 2py1 2pz1

Wednesday:

Bonding

Electronegativity

Dipole moments

Formal charges

Structural formula

Resonance